2-Aminoadamantane hydrochloride → 2-Isocyanatoadamantane

HRID 72120Notes

Reaction equation

HRID 72120 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:13]([O-])(O)=[O:14].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:10]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]([CH2:5]3)[CH:3]1[N:2]=[C:13]=[O:14])[CH2:9]2

Participants

5

Reactant 3

HCID 253312-Aminoadamantane hydrochlorideHCID 94429TriphosgeneHCID 516892Sodium Bicarbonate

Product 1

HCID 128826302-IsocyanatoadamantaneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vigorously stirred mixture of 2-aminoadamantane hydrochloride (5.01 g, 26.7 mmol), CH2Cl2 (50 mL) and satd aq NaHCO3 (50 mL) was cooled in an ice bath. After 15 min, solid triphosgene (2.64 g, 8.9 mmol) was added. The mixture was stirred in the ice bath for 30 min and the layers were separated. The aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to afford the title compound (3.55 g, 75%) as a white solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (100 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4c317ed86d34d8ea3cd71d10c35d13c
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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